


Candies, Crushes, and Confessions

by deanbaby



Category: Supernatural
Genre: Alternate Universe - High School, Dean is shy, Destiel - Freeform, Jock!Dean, Kissing, Love Letters, Lunch Dates, M/M, Valentine's Day Fluff, cuteness, nerd!cas, seniors, valentines day surprises
Language: English
Status: Completed
Published: 2015-02-14
Updated: 2015-02-14
Packaged: 2018-03-12 19:58:46
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,234
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3353426
Author URL: https://archiveofourown.org/users/deanbaby/pseuds/deanbaby
Summary: <blockquote class="userstuff">
              <p>Dean's had a crush on Castiel for a long time, and he finally got up the courage to do something about it. </p><p>~7k of pure fluff ensues</p>
            </blockquote>





	Candies, Crushes, and Confessions

**Author's Note:**

> Rated teen and up for some language. Not a lot, though. Enjoy!!!

**Monday**

Dean triple checked the hallway, glancing in both directions before slipping the flat piece of paper through the little vents of Castiel’s locker. He let out a nervous sigh, running his sweaty palms on the front of his shirt. Dean heard the bell ring, and the classroom doors opened as kids filed out into the halls.

He ducked behind the corner, waiting for Castiel to come and open his locker.

About five minutes later, Dean almost gave up, the late bell had rung and Castiel was still nowhere to be seen. He took a step in the direction of the class he was supposed to be in, but stopped abruptly when he saw a tall, adorable, messy haired figure walking towards him, predictable bottle of Cherry Coke Zero in his hand. He had a pass of course, he would never be out in the halls late without permission.  Castiel turned at his locker, giving Dean a chance to admire him. He was wearing a tightly fitted flannel, blue, with khakis that were slightly too short and sneakers that were worn from use.

When he turned to the side, Dean could see that his glasses were slipping down his nose like always. He smiled.

His grin was immediately wiped off of his face when Castiel found the note, quickly read it, frowned, and then proceeded to throw it away in the garbage after he closed his locker.

Castiel didn’t like the note? Why? Dean only put nice things on it, of course. He tried to think of something that he wrote that may have triggered that reaction from him, but his mind went blank.

_Dear Castiel,_

_I think you’re really cute. You always read and when you get really into a book, your face shows the emotions that you’re feeling. I think it’s adorable. You’re not in any of my classes except lunch because I’m just average and you’re taking AP, but I wish I was. Maybe I’ll talk to you in person someday._ ♥♥♥

_\--Your Secret Admirer_

He wanted it to be clear that he liked Castiel, but not come off as creepy or stalkerish. Maybe Castiel didn’t like that the note wasn’t signed.

Yeah, that’s it. He probably wanted the person to man up and reveal who they are, not hide. But, he couldn't do that just yet.

**♥♥♥♥♥♥**

 

Castiel felt like crying. He hated getting made fun of, and someone sending fake love notes to him really fucked with his head. He was embarrassed. He already knew that nobody was going to be his Valentine, those jocks didn’t have to throw it in his face. It was probably one of them who sent the note as a joke. He slumped down in his chair.

**  
♥♥♥♥♥♥**

 

**Tuesday**

****

Dean slipped the note in Cas’ locker again and waited for him. This time he thought he did a better job with the note.

****

_Dear Castiel,_

_Sorry for not signing my name. I’m just scared you won’t like me back. I promise I'l_ _l tell you on Friday. Hopefully then you’ll know who I am and you might be my Valentine and go on a date with me on Saturday, Valentine’s Day._

 _P.S. Your hair looks really nice today._ ♥♥♥♥♥♥

_\--Your Secret Admirer_

_**** _

Dean liked the note better than the last. He even drew more little black hearts than the last one. He hoped Castiel wouldn’t figure out that it was him. That would ruin the surprise and his big plan.

****

Dean felt his heart stop when Castiel frowned again after he read the note. He wasn’t just a little annoyed or sad or whatever the first frown meant, he seriously looked like he was going to cry.

****

This time, Castiel crumpled the note up before throwing it away. Dean watched him disappear behind the corner before he slumped down the lockers. _What_ was wrong with his notes?

****

♥♥♥♥♥♥

****

His hair? _Seriously_? Castiel ran his hands through it in the bathroom, looking in the mirror. He didn't have time in the morning to try to fix it. The ends were sticking up all over the place.

****

_Damn it._

_**** _

And now Castiel knew that they were going to reveal themselves on Friday. Does that mean on Friday he’s going to get beat up? Probably. Castiel sighed and went back to class.

****

♥♥♥♥♥♥

 

**Wednesday**

****** **

Dean decided to step it up with today’s letter.

****** **

_Dear Castiel,_

_Tomorrow is my last note. On Friday I have this big thing planned for you, if you’ll accept it. I really hope you don’t hate me. You’ve thrown away my last 2 notes. I know I should tell you who I am, but it’ll all happen on Friday. Just please know that I really like you a lot._

_P.S. You make my heart go wild when I see you with Coke for some reason. It’s a weird thing. Sorry._ ♡♡♡♡♡♡♡♡♡♡♡♡♡♡♡♡♡♡♡♡

_\--Your Secret Admirer_

_****** ** _

Dean waited in the same corner as the past two days and watched as Castiel opened his locker. He tugged at the hem of his team football t-shirt in anticipation. This time Castiel didn’t throw it away. He was still frowning, but he tucked it into the top shelf of his locker before shutting it and walking away.

****** **

He had to bite his lip to keep from howling in happiness. This meant that he had a chance. Well, sort of. Dean hadn’t even given him the invitation. He could still decide not to come. But, Dean didn’t care. He was still going to set up everything he had originally planned for Castiel, all the grand gestures that he was going for from the start. It was going to be amazing.

****** **

♥♥♥♥♥♥

****** **

Castiel didn’t know what was going on. There was going to be a surprise? Did that mean he was going to get ambushed or something? He shouldn’t fall into the trap of whatever this person was going to set up for him.

****** **

And what if it wasn’t a trap? What then? Castiel actually has an admirer. What a thought.

 ********  
**** ♥♥♥♥♥♥

 

**Thursday**

 

Dean was _so_ nervous. He had one note left, the one that would tell Cas to meet him up.

******** ** **

_Dear Castiel,_

_So, this is my last note. I just wanted to say that I really, really, really like you. Like, really. I was just making sure you knew that._

_I have a little something planned for you, tomorrow after school. Could you go into the gym about 15 minutes after the final bell rings? That way we can be totally alone. Just me and you. If that creeps you out or you think I’m going to kill you or something, I promise I won’t. I might want to hold your hand. But not if you don’t want to._

_Sorry, I’m going on. It would be really cool if you would stop by, or something. I won’t tell you anything more. I really want this to be a surprise. Just give me a chance. At least think it over? Please? I can’t stop thinking about you. I hope I don’t sound too desperate._

_Also just a side note------ You looked really cute this morning. I like it when you wear those silly t-shirts with science puns that I barely get. Maybe one day you can explain one to me?_

_\--Your Secret Admirer_ ❤♥♥♥❤♡♡♡❤♥♥♥❤♡♡♡❤♥♥♥❤♡♡♡❤♥♥♥❤

******** ** **

Dean really went all out with those hearts.

******** ** **

♥♥♥♥♥♥

******** ** **

Castiel didn’t know what to do. Should he go to the gym? What if there’s someone there to hurt him? He couldn’t think of anything he’d done to make anyone go through such an elaborate process just to hit him. Like, sure, he was a nerd, but it wasn’t like he talked down to anyone or made them feel inferior because they just didn’t test well. He was just overreacting, nobody had even hurt him other than a few times when he got shoved into a few lockers.

******** ** **

Not inside, them, no. Just slammed into the outside. He was far too big to fit into one of those small spaces.

******** ** **

And what if it wasn’t a set up? What if on the other side of those gym doors would be a cute boy waiting for him? What if he likes Castiel and wants to be his boyfriend?

******** ** **

Yeah, _right_.

******** ** **

Castiel sighed, glad that the final bell just rang and he was allowed to go home. He would make his decision later.

******** ** **

♥♥♥♥♥♥

 

**Friday**

******** ** **

Dean took a look around him. He spent four hours setting this up, getting use of the gym from the gym teacher who let Dean do whatever he wanted because he was a star football player, and passes from his teachers because he told them he needed to work on a project. Technically, it wasn’t a lie. This was quite a project.

******** ** **

There were red and white lights hung from the bleachers, going around all sides of them. He put red, pink, and black hearts all over the gym walls. There were two rows of white and pink flowers that started at the door and formed a path to the middle of the gym, where Dean stood, in the center circle of the basketball court. Around the line of the center circle, where Dean had won many tip offs in his basketball games, he had placed about 24 bottles of Cherry Coke Zero, something that Castiel always had in his hands.

******** ** **

Dean turned around, his back facing the gym doors as he clutched the box of caramel filled chocolates to his black-sweater-with-a-red-heart-on-it covered chest. He had wanted to turn the gym lights off to give the colored lights more of an effect, but when he did, it went completely black, even when his lights were lit. So, they were just there for a romantic feeling.

******** ** **

He checked the time on his phone. 3:16. Castiel should be here any minute.

******** ** **

If he was coming at all.

******** ** **

Before Dean had a chance to get himself down about that thought, he heard the gym doors open. He whirled around, facing whoever it was.

******** ** **

Dean couldn’t help the idiotic grin that was permanently plastered onto his face when he realized that messy hair, those long legs, and the plain graphic tee that Castiel was wearing. He was a little confused when Castiel stopped at the door, seemingly frozen. He looked around, apparently taking in the scenery.

******** ** **

Keeping his head down, Castiel followed the flower path to where Dean was standing in the center. Dean didn’t breathe until Castiel was standing right in front of him, head still down. He let out a puff of air.

******** ** **

“I didn’t think you would come.” Dean breathed out. He felt his palms get sweaty because Castiel was standing right there. Right there, in front of him, in the gym, right _there_.

******** ** **

“I wasn’t planning on it.” Castiel finally raised his head to look Dean in the eye.

******** ** **

“Oh. Okay.” Dean didn’t know what else to say. “I’m De--”

******** ** **

“Dean. I know. You’re… popular. And you wear football jerseys and I thought you had a girlfriend.” Castiel tucked a loose strand of hair behind his ear. Dean almost melted. Castiel knew his name!

******** ** **

Except, wait, girlfriend?

******** ** **

“I don’t have a girlfriend. At all. I’m not interested in anybody right now. Except, you know, you.” Dean felt his face get hot. It was one thing to write an anonymous note saying how much he liked Castiel, but a completely different thing to say it out loud to his face.

******** ** **

“What about that girl you’re always with? Carly? Something like that. She has beautiful red hair and she always holds your arm.” Castiel tried to describe her.

******** ** **

“Oh, you mean Charlie?” Castiel nodded. “Cas, she’s just a friend. Really. I mean, she has a girlfriend.”

******** ** **

He looked embarrassed. “Oh, sorry. But, Cas?”

******** ** **

“Sorry. I didn’t mean to call you that, it just sort of slipped out. I can call you Castiel if you want.” Dean wanted to smack himself in the face for being so fucking stupid.

******** ** **

“It’s okay. I don’t care.” Cas looked around him again. “Is this all for me?”

******** ** **

“Yeah, I finished about a half hour ago. Do you… do you like it?” Dean asked. He really did work hard on it.

******** ** **

“It’s amazing, Dean. Really, it sort of feels like I’m in a Valentine’s Day wonderland. So, you’re the one who’s been sending me those love notes?” Cas asked.

******** ** **

“Uh, yeah. I just… didn’t know how else I could get you to come here. I was too nervous to talk to you in real life. But then you threw them away and I didn’t think you were going to come. So, sorry, I guess.” Dean awkwardly shoved the box of chocolates into Cas’ chest. “These are for you.”

******** ** **

Cas took them from Dean. “Th-thank you. I- the only reason I threw them away was because I thought they were fake. And you’re ridiculous if you think you couldn’t talk to me. You’re Dean Winchester! You can talk to anybody. Everybody loves you. When I walked in here, I couldn’t believe it was you. You’re way too...  cool to be talking to me.”

******** ** **

“Says who?” Dean challenged.

******** ** **

“I don’t know. Society? I’m kind of a loser. Won’t your friends make fun of you?” Cas asked.

******** ** **

“They don’t care. My best friend, Benny, helped me plan all this in the first place. I’ve been, in his words, ‘fawning’ over you, since sophomore year. I think you’re perfect. I just haven’t gotten up the nerve to talk to you. I mean, you’re so smart and everything and I just get okay grades and I was so nervous about doing all of this because I thought you were going to reject me. I mean, you still might reject me but you haven’t so far. So that’s a good sign.” Dean rubbed his hands together. He didn’t know what he was supposed to do.

******** ** **

“Is this for real? You really like me?” Cas asked.

******** ** **

“I do. I really, really do.” Dean answered honestly. He couldn’t even begin to tell Cas how much he liked him. “Is that good?”

******** ** **

“It’s… great.” Cas smiled, and Dean noticed a faint blush creep up onto his cheeks. “Nobody’s ever had a crush on me before.”

******** ** **

“Well, I’ve never spent four hours decorating a school gym and standing at three different vending machines an hour before school starts so that I can have enough Cherry Coke Zeros to fill the circle for somebody who I honestly didn’t think was going to even come. There’s no more Coke in any of the vending machines, and I think the janitors hate me now.” Dean’s hands began to feel even sweatier as he got more and more nervous and he stuffed them into his pockets so Cas wouldn’t notice.

******** ** **

Cas looked around the center circle, confused about what Dean was talking about when his face lit up after he saw what Dean had done.

******** ** **

“How did you know that those were my favorite?” he asked.

******** ** **

“I see you with one everyday. It wasn’t hard to guess.” Dean replied. He shifted from foot to foot.

******** ** **

“So, uh, Cas, the whole reason I brought you here was so I could ask you something. I just wanted to wait and see if you even liked me. If you were even going to come. But you did. Do you even like me? Like, not even as a date. Just in general.” Dean asked, suddenly feeling extremely vulnerable. Cas could completely turn him down right now and leave and he would be left alone again.

******** ** **

“I’ve never thought about it before. I mean, you’ve always been that popular guy that everybody had a crush on. I just assumed you’d never give me a second look.” Cas adjusted his book bag on his shoulder.

******** ** **

“Trust me, I’ve been finding excuses to walk by you in the cafeteria, just so I could see your face for two seconds.” Dean admitted. He was annoyed with himself for waiting and waiting to ask Cas the question he’d been wanting to ask since sophomore year.

******** ** **

“Cas, will you be my Valentine?”

******** ** **

Once he asked it, he realized that it may have sounded like he just wanted Cas for a day, when in reality, he wanted Cas for as long as he could have him.

******** ** **

“I mean, and also my boyfriend. Or date, or something, Whatever you’re comfortable with, I just want you--”

******** ** **

“Yes, Dean. I would love to be your Valentine. Or boyfriend. Or date.” Cas answered.

******** ** **

Dean almost melted when he saw that Cas was blushing.

******** ** **

“Yeah?” was all he could choke out, because, seriously? The planets were aligned and a star just exploded and Cas said yes to him.

******** ** **

“Yeah.” Cas smiled.

******** ** **

“Do you have something going on tomorrow? I was planning on taking you out if you said yes. It’s okay if you can’t, we can reschedule or something….” Dean trailed off.

******** ** **

“I have nothing to do. I’m looking forward to it. Although, I don’t know how you’ll be able to top this.” Cas said, gesturing around the gymnasium.

******** ** **

“I have some ideas.” Dean replied.

******** ** **

It was a total lie. He had no idea what he was going to do. To be honest, he didn’t even think that Castiel was going to go to the gym, let alone say yes to him. He really needed to start thinking….

******** ** **

“So, what now?” Cas asked.

******** ** **

“Uh, I don’t know. I mean, we have the gym until 5:00 when the school closes, so we can stay here and talk, I guess. Unless you want to go home or something. That’s cool, too.” Dean left it up to Cas.

******** ** **

“I wouldn’t mind staying, if you don’t, either. It would be nice to learn more about you.” Cas shrugged like it was nothing.

******** ** **

“Then, let’s stay. I don’t have anywhere to be besides here with you.” Dean said.

******** ** **

They both just sort of stood there until Dean got up the nerve to grab Cas’ hand and drag him down to the ground. Cas set his bookbag and his new box of chocolates down and crossed his legs, Dean mirroring him.

Dean noticed Cas shiver slightly. “Are you cold?” he asked.

******** ** **

“I’m fine, really it’s just a little chilly in here,” Cas replied, but Dean as already running to the other side of the gym, picking up his backpack from the corner, and yanking out his jacket for Cas to put on. He sprinted back over by him and plopped it down in his lap, going to sit on the ground again. “uh, thanks.”

******** ** **

Dean smiled, leaning back.

******** ** **

“Can I open one of these?” Cas asked, pointing to the circle of Cokes.

******** ** **

“Whatever you want, they’re all yours.” Dean answered.

******** ** **

He watched fondly as Cas reached to the side and grabbed two bottles, handing one to Dean. Dean set it back down on the floor, holding his hands up. “These are for you, not me.”

******** ** **

Cas pushed it back towards him. “And I want you to have it.”

******** ** **

Dean picked the bottle up and opened it, but only after Cas had.

******** ** **

“Dean… this is your letterman.” Cas’ voice sounded so soft compared to the rougher, deeper sound it usually was.

******** ** **

“Yeah, and I want you to wear it.” Dean answered.

******** ** **

“But, I thought you never gave it up for people. It was like, a thing that you just didn’t do.” Cas looked confused.

******** ** **

This was true. Dean was too proud of getting that letterman to let anybody else wear it. “I made an exception.” Dean took a sip of the Coke.

******** ** **

“Well, thank you.” Cas replied.

******** ** **

Dean noticed that Cas’ thick rimmed glasses were starting to slide down. Before he could stop himself, he had scooted closer and pushed them back up his nose. Dean realized that he was just inches away from Cas. They were breathing the same air.

******** ** **

Dean had another one of those odd, unexpected, and random bouts of courage that he’d been having all day, and lean in just a bit to where he was close enough that he could plant a soft kiss on the side of Cas’ nose.

******** ** **

“Sorry.” Dean blushed, ducking his head.

******** ** **

“No, it’s okay. Thank you. My glasses are annoying, they’re too big and they always slide off.”

******** ** **

Dean looked up at Cas, about to say something, but the words were gone from his lips as soon as he saw how red Cas’ face was.

******** ** **

“You’re blushing.” Dean pointed out.

******** ** **

Wow, Dean. Breaking news. I’m pretty sure he fucking knew that already. Jesus.

******** ** **

“Yeah, I know. I’ve never been kissed before and I can feel how hot my face is.” Cas fanned himself with his hand. “I was trying to act all cool and like it didn’t effect me but on the inside I felt like I was dying. And I guess it showed on the outside, too, so that’s awesome.”

******** ** **

Dean laughed, covering his mouth with his hand.

******** ** **

“You’re really cute.” Dean told him.

******** ** **

“Thank you. You’re very sweet.”

******** ** **

♥♥♥♥♥♥

******** ** **

Dean turned off the car and sat back in his seat.

******** ** **

Today was one of the best days of his life.

******** ** **

They sat and talked and drank Cherry Coke and ate chocolates, or Cas did, Dean didn’t want any-- he bought those for Cas, not himself, until 5:30 when they got kicked out by the janitors.

******** ** **

He insisted on taking Cas home since he didn’t go home on the bus and he had to stop himself from screaming when he walked Cas to the door and gave him a goodbye kiss on the cheek. Dean insisted that he kept his jacket, he could just give it back whenever. Dean promised that he would pick Cas up at noon to have lunch and whatever else he wanted. They exchanged numbers and Dean put him in as Cas <3\. He knew that it was going to be the best first date ever.

******** ** **

Dean got out of the car and walked up the front steps of his house, opening the door. The picture he saw wasn’t surprising. Sam was sprawled out on the floor with a bunch of papers and books all around him, and Dad was behind him on the couch, reading a manual on how to fix the dishwasher.

******** ** **

“Hey, I’m home.” Dean announced.

******** ** **

Sam bolted up from where he was lying and was at Dean’s side in a second.

******** ** **

“You were gone for a while. Does that mean he said yes?” Sam asked.

******** ** **

Dean blushed. “Yeah, he said yes. I’m taking him out to lunch tomorrow.”

******** ** **

John put his manual down and stood to pat Dean on the back. “Good. I’m proud of you, son. It takes a lot of guts to put yourself out there like that, way to go. You’d better treat him right. And I expect to meet him in two weeks. Deal?”

******** ** **

“Deal.” Dean agreed. “And just so you know, I plan on treating him like the king that he is.”

******** ** **

John made a sound of agreement, which Dean took happily.

******** ** **

“How was it? Did you kiss him?” Sam pushed his long hair back from his forehead.

******** ** **

“On the nose and on the cheek.” Dean answered.

******** ** **

Sam just smiled, satisfied with Dean’s reply, and he sank down onto the floor again, picking up a book and starting to read.

******** ** **

“Okay, then. I’ll be in my room, I’m gonna go call Benny and make plans for tomorrow.” Dean said before he walked up the stairs and closed his bedroom door behind him. He pulled out his phone and found Benny’s number, pressing the call button and holding the phone to his ear. Benny picked up on the second ring.

******** ** **

“Hey, brother. Any broken hearts?”

******** ** **

“None here. Cas said yes, I get to take him out tomorrow.” Dean told him. It was hard to keep the smile out of his voice.

******** ** **

“Way to go! When are you going to introduce him to your friends? By the way you’ve talked about him, I expect nothing less than an angel.” Benny teased.

******** ** **

“Oh, he is. And I don’t know, maybe just you and Charlie and Kevin. Garth, too. Some of the other guys on the team are kind of rude, like Luc and Roman, and I don’t want him to get the impression that I’m really like that.” Dean reasoned.

******** ** **

“I hear ya,” Benny said. “do you have anything planned?”

******** ** **

“No, not yet. I’m going to call Charlie and ask what she thinks. Then I’ll probably try to call the diner and see what Ellen can do for me.” Dean answered.

******** ** **

“Smart. Alright, Dean. I’m gonna let you go make your fancy date plans-- remember to tell me all about it on Monday.”

******** ** **

Dean smiled. “How could I forget? Bye, Benny.”

******** ** **

Dean waited to hear a deep-voiced see ya, brother, on the other line before he hung up.

******** ** **

He sat down on his bed and put his bag on the ground. Dean didn’t have any homework that weekend and didn’t plan on opening it for the next two days.

******** ** **

Dean laid back, kicking his shoes off and putting one arm behind his head, the other holding the phone to his ear.

******** ** **

Dean smiled when he heard the bright, familiar, “Hey, Dean!” coming from Charlie.

******** ** **

“Hey, yourself. I got a question.” Dean started.

******** ** **

“Ask away.”

******** ** **

“I need to do something really romantic for Castiel. Something that will make him blush so hard that he melts and smile so wide that his face hurts. Any ideas?” If anyone knew anything about romantic stuff, it was Charlie. She never did any of it herself, but she thought it was adorable when other people did.

******** ** **

“Like, even more romantic than the show you set up in the gym today?”

******** ** **

“Even more.” Dean replied.

******** ** **

“Hmmmm,” Charlie thought. “Call Ellen at The Roadhouse. Tell her you want the Deluxe Valentine Special, and that Charlie told you about it. Don’t ask any questions. Just do it. I promise you won’t regret it.”

******** ** **

“Uh, okay, thanks.” Dean said, unsure about the shadiness this required for Valentine’s Day.

******** ** **

“I gotta go, Dorothy’s calling me. Good luck!” Charlie hung up.

******** ** **

Dean smiled at her quirkiness. He sighed, a little tired from making a ton of phone calls, but started dialing the number for The Roadhouse before he forgot what Charlie said.

******** ** **

“Hello?” A slow voice answered.

 

“Ash, put Ellen on the phone. It’s Dean.” he told him.

******** ** **

“Alright, man.”

******** ** **

Dean hears some shuffling and scratching on the other line before he heard Ellen’s motherly voice.

******** ** **

“What can I get ya, Dean?” she asked.

******** ** **

“Uh, the Deluxe Valentine Special?” Dean hesitated before adding, “Charlie told me.”

******** ** **

“You sure?” Ellen checked.

******** ** **

“I think so,” Dean said, sounding unsure of himself.

******** ** **

“What time are you coming to the restaurant?”

******** ** **

“Around noon was the plan. Is that okay?”

******** ** **

“Perfect. I’ll see you then. And, Dean, I want to meet that person you’re bringing over.” Ellen said, as if she wanted to meet him a long time ago and was annoyed that Dean didn’t introduce them.

******** ** **

“Sure thing.” he told her.

******** ** **

“They hung up the phone with goodbyes and Dean closed his eyes. He really hoped that whatever was going to happen at The Roadhouse would be good enough for Cas.

******** ** **

♥♥♥♥♥♥

******** ** **

Dean went through the rest of his evening in a red and pink haze. All he could think about was Cas and their date and how he needed everything to go perfectly.

******** ** **

After dinner, Dean ran into his room and opened his closet, throwing every pair of nice jeans he had on his bed, along with all of his red and white shirts. He thumbed through everything, trying to decide what to wear. His red and black flannel? Or the pink long sleeve from last year’s Valentine basketball tournament? Or maybe his white henley? His black t-shirt with the pink stripes?

******** ** **

Dean settled on a mostly red flannel with white mixed in that created a light pink where the colors crossed. He carefully folded the shirt and placed it on top of his dresser.

******** ** **

What about jeans? Dark wash? Light wash? Ripped? Should they be worn in or faded? Relatively new?

******** ** **

Dean threw the ones with rips and permanent grass stains from too much roughhousing with Sammy back into his closet.

******** ** **

After deliberating for about seven whole minutes, he decided to go with the long, plain dark wash jeans. They were tight enough that they showed off his thighs, but not so tight that they were ridiculous looking skinny jeans.

******** ** **

Satisfied, Dean cleaned up his mess of clothing and sat back down on his bed.

******** ** **

Shoes.

******** ** **

He looked to the corner of his room where he kept all of his shoes. He had two pairs of converse--red and black, a pair of yellow construction boots, a pair of black combat boots, and a pair of brown combat boots. All of his running shoes and basketball shoes and football cleats were stuffed in a bag somewhere in the basement. He didn’t have to get them out until summer.

******** ** **

Dean decided on the brown combat boots. He didn’t wear them often and they looked somewhat new.

******** ** **

He laid back, tired from the day, but excited for the-- hopefully-- long day tomorrow.

******** ** **

♥♥♥♥♥♥

 

********Saturday, Valentine's Day********

 

Dean rang the doorbell and put his hands behind his back politely. When the door opened, Dean expected to see Castiel, but instead he saw a shorter man with hair past his ears and honey colored eyes.

******** ** **

“Cassie!” The man called behind him, towards the staircase. “A tall man is here to see you!”

******** ** **

Dean blushed, but forgot all about his embarrassment when he saw Cas come down the stairs, pushing his glasses up the bridge of his nose.

******** ** **

“Thanks, Gabe.” he told him.

******** ** **

The man, Gabe, left at Cas’ words, giving him a wordless pat on the back.

******** ** **

Cas was wearing a simple red sweater with a white collar shirt underneath it. His jeans were dark and straight and his plain black Vans looked amazing on him. Dean’s only complaint is that his hair is barely messy, with only a few wild loose strands.

******** ** **

“Hey,” Cas said. “That was my older brother. He’s home to visit for a little while.”

******** ** **

“Hey,” Dean nodded at Cas, “that’s cool. I have a little brother, Sam. He’s a freshman. Are you ready?”

******** ** **

“Yeah. Sorry, I thought you would text me or something to come out.” Cas ran his hand through his hair before he stopped abruptly and closed his eyes, cursing at himself.

******** ** **

“What’s wrong? Did you forget something?” Dean asked.

******** ** **

“I smoothed my hair down. And then I just ruined it right now.” Cas explained, taking his hand away from his head. “Can you like… fix it?”

******** ** **

Dean pursed his lips. He could either smooth it back down or….

******** ** **

“Hey!” Cas exclaimed when Dean ruffled his hair up with both hands. He tried to get his fingers all around Cas’ head for maximum effect.

******** ** **

“What? I love it when you’re hair is messy. To be honest, I was a little disappointed when it was all tame. Do you hate me?” Dean asked. He hoped fucking with Cas’ hair wasn’t a deal breaker. He just took the opportunity and ran with it.

******** ** **

“No, I don’t hate you,” Cas laughed, “do you really think my hair looks good when it’s all messed up like that?”

******** ** **

“I think it looks amazing. Really, Cas.” Dean told him earnestly.

******** ** **

“Thank you. We can go now. I like your boots, by the way.” Cas complimented him.

******** ** **

Dean smiled, glad that he picked the brown boots.

******** ** **

♥♥♥♥♥♥

******** ** **

Cas and Dean ate normal burgers and fries, sipping on Cherry Coke Zeros and talking about everything. Dean thought the date was going pretty well. He was just a little confused on when the Valentine thing was gonna happen.

******** ** **

He totally forgot about it.

******** ** **

“Here you boys are,” Ellen said as her and Ash started loading the table with things. Dean didn’t bother to look, it was probably just refills of their drinks and he was too entranced by just… Cas.

******** ** **

Cas looked confused. “Sorry, we didn’t order anything else, ma’am.”

******** ** **

Dean realized that it probably had something to do with what he told Ellen last night.

******** ** **

“Uh, Cas, I got us something different. I hope you like it, to be honest I don’t even know what it is.” Dean told him, hoping that he wasn’t mad that Dean did something without asking if it was okay. What if he had an allergy that Dean didn’t know about?

******** ** **

“Oh, it’s oka--” Cas stopped himself. He was staring wide eyed at the food in front of them. Dean didn’t have time to look, he was too busy watching Cas’ eyes, but he finally let them out of his sight and he looked down at the plates that Ellen kept piling on.

******** ** **

It was definitely the Deluxe Valentine Special.

******** ** **

There were plates and plates of red and white and pink food. Each plate had a different treat on it. There were chocolate covered strawberries, heart-shaped watermelon slices, red velvet cupcakes, cherry pie, white chocolate pretzels, raspberries and pink whipped cream, strawberry milkshakes, pink rice krispie treats, little heart-shaped rolls, and cheesecake with cherries on top.

******** ** **

Ash gave them red napkins with hearts on them and fancy glasses that Ellen filled up to the brim with pink lemonade and Cherry Coke Zero, which she put extra cherries in just for Cas.

******** ** **

They both left with a polite, “Enjoy!” and Ellen gave Dean wink. Cas was still staring at the table.

******** ** **

“Dean?” he said, confused and in awe and clearly not knowing what to do.

******** ** **

“Okay, so I have an explanation. I swear.”

******** ** **

Cas nodded. “I’m listening.”

  
“I was excited about you saying you wanted to go out with me, so I called my friend Benny who was happy for me and stuff but suggested I do something like I was already thinking, and then I called the ‘beautiful redhead’, Charlie, and she told me to call Ellen at the diner and say that I wanted the ‘Deluxe Valentine Special’, and I did, not knowing what this entailed. And I guess this is it.” Dean explained. He sort of regretted telling Cas that he told two people, because it might not have been okay with him.

******** ** **

Cas just laughed. “Seriously? That’s so funny!”

******** ** **

Dean let out a sigh of relief. “I’m so glad you’re not upset with me. I would have been so mad at myself if I screwed this up already.”

******** ** **

“Why would I be mad?” he asked.

******** ** **

“Uh, because I told two people about us before I even knew that it was okay to do that, and maybe you weren’t comfortable with it. I didn’t know if you wanted to be public or not.” Dean said.

******** ** **

“I mean, yeah. I guess I wouldn’t mind it. People don’t pay attention to me, anyways, but I guess they would if I was holding your hand.” Cas blushed at the his own mention of them holding hands. “I was actually thinking you would want to keep it under wraps. Which now as I think back on it is not a very smart thought after that grand gesture you pulled yesterday.”

******** ** **

“Cas, I don’t care if people pay attention to you or not. I’ve been not so secretly pining over you since sophomore year when you moved here. I don’t want to hide you now that I’ve got you. Do you want to sit with me at lunch on Monday? You don’t have to, it’s just that I know all my friends want to meet you.” Dean offered. He really would like Cas to sit with him. Not just on Monday. For as long as he could have him.

******** ** **

“Okay. Okay, I’ll think about it. Thank you. So, we’re good”

******** ** **

“All good here,” Dean smiled at him, “so what are we waiting for? Let’s eat!”

******** ** **

♥♥♥♥♥♥

******** ** **

Dean went home that night with a permanent smile on his face.

******** ** **

He took Cas home, holding hands in the car on the way back, walking him to the door and watching as he closed the door behind him, but not before he gave Cas a light, chaste kiss on the lips. He didn’t miss the crimson blush on his cheeks as he went inside.

******** ** **

Dean felt like he was floating as he drove himself home. He just sort of collapsed when he stepped inside his house, getting the attention of Sam.

******** ** **

“Is this a good collapse or a bad collapse?” Sam asked him. His voice sounded like a million miles away.

******** ** **

All Dean could do was give him a thumbs up. Sam seemed satisfied with that, he bent down to give Dean a solid pat on the back, which he barely felt, and left the room.

******** ** **

Dean just laid down like that, full from lunch and all of that wonderful food. The only reason he ever moved from his comfortable spot on the floor was because he took out his phone to text Cas because they really were out late, it was almost 10:00 PM and they left at around noon for lunch.

******** ** **

He almost melted when he saw that there was already a text from him.

******** ** **

**Cas <3: Happy Valentine’s Day, Dean. I had a great time.**

**Dean: Happy Valentine’s Day to you, too. I’m really glad you had fun. Maybe we can do it again sometime?**

**Cas <3: Definitely. Maybe not so extravagant next time?**

**Dean: I guess I can take it down a notch or two.**

**Cas <3: Sounds good.**

**Dean: I’ll see you Monday?**

**Cas <3: See you Monday.**

**Dean: Have a good weekend :)**

**Cas <3: You, too ;)**

******** ** **

♥♥♥♥♥♥

******** ** **

**Sunday**

******** ** **

If on Sunday Dean called Benny because he was so excited about his amazing date with Cas that he couldn't wait for Monday, then nobody had to know.

********  
** ****** ** **

♥♥♥♥♥♥

  
  
**Monday**

******** ** **

Cas was sitting by himself at lunch, working on a math problem. He knew that he could take Dean up on his offer to sit with him, but some of his friends, admittedly, were intimidating. Especially the big one, Benny.

******** ** **

It wasn’t like he was ever mean to Cas, no, he was probably a sweetheart, if he was Dean’s friend. It was more like he just looked like he could beat the crap out of anyone who messed with his crew. And that was just a little scary.

******** ** **

He was about to move onto his AP Literature assignment when someone sat down in front of him.

******** ** **

“Hey, Cas. Can I sit here?” Dean asked.

******** ** **

“Ah, uh, yeah, sure. I mean, yeah.” Cas moved some of his papers so Dean had room to set his lunch tray on the table.

******** ** **

“Cool. Can some of my friends come over, too?” Dean looked down and saw that Cas had all of his school stuff on the table. “Actually, nevermind. You look busy.”

******** ** **

“No! No. It’s okay. Really. I can just do this later.” Cas told him. He could, actually, do it later. He didn’t have anything going on after school.

******** ** **

“Yeah?”

******** ** **

“Yeah.” Cas started shoving binders and books into his backpack, zipping it up and putting it under the lunch table. He saw Dean wave to someone behind him that he couldn't see, and he turned around to see a large group of teenagers walking towards him, lunches in hands.

******** ** **

Benny sat down next to Cas, Charlie next to Dean. About a dozen other kids that Cas didn’t know filled into the rest of the table. He looked over all of their faces, trying to recognize them. He knew that they were popular, but he’d never learned their names or talked to them before.

******** ** **

Cas took a sip of his Cherry Coke Zero nervously.

******** ** **

“Let me introduce you to everyone.” Dean said, standing up. He placed his hand on the redhead’s shoulder. “This is Charlie, as you know, and that’s Benny, and here we have….”

******** ** **

Dean went on to introduce him to sixteen total people. He learned that the dark haired girl next to Charlie was her girlfriend, Dorothy. Kevin was totally smart but he wasn’t in any of Cas’ classes, Garth played soccer with Ash who worked at the diner they were at, Jo is the daughter of the lovely woman to who had served he and Dean on Saturday, Ruby and Meg were the boys’ cheerleaders, Lisa and Dean had a thing before (but Benny assured him that it was so over), Gadreel played football with Dean, Adam was dating Michael and they had been together for six years--since they were eleven and they were ridiculously cute, Pam was on the speech team and wanted to be a tattoo artist, Anna played tennis, and Balthazar moved here two years ago from England. Cas scanned the faces of everybody, trying to remember them.

******** ** **

“It’s nice to meet you all.” Cas told them all. He didn’t know what else to say. He looked up at Dean and relaxed after seeing the happy smile on his face.

******** ** **

They spent the rest of the lunch period ‘getting to know Cas’. Everybody wanted to know all about him. It was weird, nobody had ever shown that much appreciation for Cas before, much less sixteen people at once.

******** ** **

He felt a little overwhelmed at the fact that all these people wanted attention.

******** ** **

Benny put his arm around Cas’ shoulders. “Don’t worry, brother. The only reason they’re acting like this is because your boy Dean, here, has been talking you up for months. Seriously, he’s head over heels for you.” Benny’s voice was deep and low, and he talked sort of slow.

******** ** **

Cas just nodded his answer. It was weird to have that many people around him actually care about what he had to say. He could get used to this….

******** ** **

♥♥♥♥♥♥

******** ** **

“So, you really don’t care?” Cas asked, clutching his books closer to his chest.

******** ** **

“Not one bit.” Dean assured him. They were walking down the hall together. Dean had tried to hold Cas’ hand, but the boy had pushed his fingers away.

******** ** **

Dean offered up his hand again, palm up, for Cas to take. His boyfriend hesitated for a second before he smiled and laced his fingers in with Dean’s.

******** ** **

If some people didn’t already know they were together, they knew now.

******** ** **

Some people looked confused at the sight of the odd couple, some looked indifferent, and some even gave them a smile and a thumbs up. They walked past Benny in the hall and Dean couldn’t hold back his grin as he saluted them.

******** ** **

Dean and Cas stopped walking when they got to Cas’ classroom. Dean let go of his hand and said goodbye, turning to walk away, but he stopped himself to whirl around and give Cas a soft peck on the lips right in the doorway.

******** ** **

“Text me later?” Dean offered.

******** ** **

Cas smiled and nodded.

******** ** **

Dean watched as his boyfriend disappeared into the classroom. His boyfriend. Dean Winchester had a boyfriend. A cute one, too. And he was really smart. And he had messy hair.

******** ** **

Yeah, I hit the jackpot, Dean thought, maybe he’ll like me so much that I can take him driving with me. Maybe he’ll come to one of my games and cheer me on. I bet he’d love Sam.

******** ** **

Cas really was amazing. And it made everything so much better that he liked his Dean’s friends, and his friends liked him, too.

******** ** **

Dean Winchester was the luckiest boy in the world.

******** ** **

♥Dear♥♥♥♥Castiel♥♥♥♥Dear♥♥♥♥Castiel♥♥♥♥Dear♥♥♥♥Castiel♥♥♥♥Dear♥♥♥♥Castiel♥♥♥♥Dear♥♥♥♥Castiel♥♥♥♥Dear♥♥♥♥Castiel♥

 ************  
  
****

**Author's Note:**

> Thanks for reading! Let me know if there's any mistakes? Please let me know what you think! Have a great Valentine's Day, you guys, much love from me <3 xoxoxo


End file.
